A Good Boy For Little Sis Pt 02

A little while later, after bathroom breaks. I am laying on my tummy, my still topless sister is smiling brightly, chatting with me about our shared taboo fetish.

"Did you ever imagine something like this would happen, Roger? My sister's voice is soft and sweet, her hand gently running up and down my back.

I turn to her as I reply, "I had lots of fantasies sis, and some dreams, but no, I mean, I had no idea you were into it."

My sis beams when she notices my cock is still fully hard. "You didn't know your little sis is a perv?"

"No, or that my little sister is the world's best cock tease," I reply.

Kate smiles, before saying, "I mean we are so lucky, You love to edge, and your little sister loves to tease cock."

"God I have been needing to tease a nice cock." Kate thinks out loud

"I couldn't tell sis," I reply sarcastically, through my moans.

Kate just smiles as I moan, smiling back at her. She places her soft hand on my thigh, right beside my hard cock.

Kate has a look of admiration as she takes in my little dick.

"That is one of my favorite things about small cocks, big brother."

"They get hard so easy and so fast, I guess there is not that much there to fill up with blood." Kate giggles as she finishes.

Kate, continues softly, a moment later. "My ex hated me teasing him about his little, or I should say, tiny dick, he has about 4 inches big bro," Kate explains.

"I mean you are actually pretty average, and nice and thick."

"I hope you can learn to be a good boy, cause I really want to suck your nice little cock bro."

"I hope I can learn too sis," I reply as she grins.

"I will suck on your little cock for hours big brother, edging you over and over," her fingers are circling my shaft, not quite touching me.

"After you learn to be a good boy for me." Kate looks me in the eyes, smiling as she finishes her sentence.I moan as a wave of pleasure shoots through my cock.

Kate's smile becomes even bigger as I respond.

"I would love to be a good boy for my gorgeous sister. I kinda like the whole small cock thing, as long as you don't make it too humiliating, okay?"

Kate kisses me softly, "No problem big brother, no problem. "Well looks like you are ready big bro."

Kate's eyes lock on my hard cock as she speaks. "Why don't you stand up big brother"?

I stand as Kate turns, so she is sitting forward, her legs together in front of her. Her eyes on mine she says, "Are you sure, Roger?"

"Yeah, yeah, I am sis," I nod as I reply, my eyes imploring her.

Kate just smiles softly before saying. "I am sorry about this part, big bro but, it has to happen, I need you to get over my knee."

"What?" I reply nervously, my head down, as my cheeks redden.

Kate smiles, "Cmon, big bro, you know what I mean, just be a good boy."

I sigh, nodding, and lay across my sister's lap. Never in my wildest dreams would I have expected the spanking I was about to get.

Kate rubs my ass lightly, making small circles. "Are you going to be a good boy for your sister?" A hard smack follows her question.

"Yes sis," I reply, three more hard spanks follow. causing me to cry out softly.

"I said, are you going to be a good boy for your sister?" Another five hard smacks follow her repeated question.

I reply through my whimpers, "Yes I am going to be a good boy for my little sister."

Smack her hand comes down on my already reddening ass, as I hear, "Good boy, just lay quietly now."

My sister spanks me again and again, counting them off with every hard spank, all the way to twenty five.

I am moaning in pain, whimpering every time I feel the sting, as her hand punishes my ass. Kate pauses for a moment, just lightly, rubbing my sore ass.

"Who owns your little cock Roger?" This time her question is followed by three hard spanks.

"My little sister, Kate, owns my little cock," I reply half sobbing now. Three more spanks reward my reply.

"Do you remember what I was wearing, the first time you got hard for your sister, Roger?" Smack, a hard spank follows the question.

"Yes sis, you were in a little white bikini, the first time I got hard for you." I reply softly, the pain, obvious in my voice. Three, even harder spanks follow.

"Do you remember the first time you jerked off for me?" she continues.

"Yes sis, I remember the first time I jerked off for my sister," I reply. Five more hard spanks follow my answer.

"Good boy, we will talk about that later." Kate is smiling brightly as she rubs my sore ass.

Kate spanks me again a series of seven hard smacks, I am whimpering, flinching in anticipation.

"Stay still, be a good boy." Kate's instructions are followed by another twenty five, counted, hard spanks.

I am sobbing softly, my eyes welling up with tears, wondering if this will ever end, and if I can take it. Consoling myself, silently, knowing it will be worth it. Kate spanks me ten more times as I lose the fight to the tears.

"Are you crying big brother?" Kate's question breaks the dam, tears begin streaming down my face, choking off my reply. Kate spanks me ten more times as I sob.

"Aww, it's okay big brother, just cry quietly and take your spanking like a good boy, most of them won't be this bad."

Kate spanks me twenty five more times, again counting softly. Her spanks become a little softer, towards the end, as I cover her legs in my tears.

"Good boy," she coos, lovingly as I sob. Kate reaches under me, giggling as she grasps my hard cock. "Still hard for your sis though, good boy," Kate gives me one last hard spank.

"Okay big bro, I think you are well on your way to being broken now, I am sorry but it did have to happen."

Kate continues her explanation. "I need you to realize, I am in charge, Your Little Sister," she emphasizes her last few words. "It turns me on to see what you are willing to go through, just to see me naked, and get teased." Kate smiles as she concludes.

Kate pulls me to her breast, allowing me to suckle as I sob quietly. "Good boy," she says soothingly as I calm.

"Do you want to continue?" Kate asks a minute later. Pulling me gently from her breast.

I nod, wiping my tears from my eyes. "Yes please sis, that really hurt, but I loved it."

Kate laughs loudly. Looking at my hardon she says, "Yeah I can see that." Kate giggles softly, before continuing. "You took longer to cry, than most of the boys I have spanked big bro."

I shake my head softly at her grin, until we both laugh.

Kate looks at her phone. "It's still early," she says happily.

"Why don't you go have a shower, I will run over to my ex's, and grab some things I need, Okay?"

I nod in reply.

"Good boy," Kate purrs, as my little cock points the way to the shower.

An hour or so later, I am again laying on my tummy, now on my bed. My sister is gently rubbing lotion into my sore, still red ass.

Kate is in her robe again. We are laughing, as she explains what happened at her ex's. After pleading with her to stay, he demanded to know what she was taking.

"His face, when I showed him what was in my bag, right in front of his friends."

"Lingerie, 3 bottles of lube, and sex toys."

"Oh My God big bro, you have no idea."

Kate laughs before continuing. "I even asked if he wanted me to leave his favorite butt plug." Kate squeals in delight, snorting as she laughs.

"I hung my titties in his friends faces, while offering them a kiss goodbye." Kate giggles as she continues, "they were both staring at my tits big bro."

"I gave both of his friends a nice little kiss, and walked out."

"While he stood there with his mouth hanging open." Kate chuckles again as I laugh.

A few minutes later, she says. "Okay big bro I want to hear about the first time I made you hard, and the first time you stroked your cute little cock to your sister."

"Hm that will be easy sis it was the same time," I chuckle, before continuing. "It was the summer after you turned 18 Kate. Remember you bought that little white bikini, that Mom couldn't know about?"

Kate smiles, softly, "I remember, you mean this one?" Kate opens her robe revealing the bikini in question.

"Yeah that one," I moan as I see the fabric hugging her perfect titties, her nice cleavage spilling out.

"See big bro, good boys get rewards, your sis always pays attention."

"Thanks sis," I reply. I smile, remembering her earlier question, as my eyes return to her magnificent boobs.

"Good boy," Kate encourages me as I stare. "I am kinda an attention whore, big bro if you couldn't tell." Kate giggles as I reply.

"I can tell sis," I turn, exposing my hard cock as proof of my statement. Kate's giggles let me know she approves.

A minute later, as our laughter subsides. Kate says, "Okay big bro tell me." She gently pushes me back down, returning her hands to my ass.

"So that summer, a lot of my friends noticed you, Kate."

"I was hearing every day about how hot you were, how nice your ass was, and how perky your boobs were."

I pause a moment, before asking, "Do you remember soy boy?"

Kate nods smiling, as I continue.

"Well he and I were talking, he understood because of Chloe."

Kate nods as I mention my friend's beautiful sister.

"He explained how I was missing out."

"How a hot little sis could be a never ending supply of spank bank material."

"I wasn't buying it, but it so happened, you and Chloe were laying out."

"Soy boy, convinced me to come to the window and check you out."

"I felt weird at first, but he kept reassuring me, telling me to think of you as a woman and not my sister."

"I started to realize you were hot Kate, your legs looked so good, and well there is no denying you have a great ass sis."

"Why thank you," Kate responds with a giggle.

"Then you made it way worse," Kate looks at me as I pause. "You rolled over sis."

Kate laughs, and tells me to roll over. I do, moaning as my sister's hand rests on my tummy.

Kate begins lightly teasing, just under my hard cock. "Go on," she says encouragingly.

"Well we stood there staring at you girls, our sisters, for a few more minutes, until he asked what I thought of the view."

"I was like, damn dude our sister's are hot. Soy boy just pointed at my tent, and said he could tell."

"I took some convincing, but not long after, we were stroking our cocks, right next to each other, staring at our hot little sister's."

Kate moans as I finish. "Wow Bro that is hot, two guys, stroking right next to each other, over their sisters." A moment later she says, "Did you guys ever do that again?"

I smile before replying, "Every chance we get sis." Kate laughs as I add, "we still jerk off together a lot."

"To your sister's?" Kate inquires, pausing to untie her bikini top, and teasingly sliding it off.

I let out a soft "Wow," before answering. "Yeah sis we watch a lot of taboo porn, and talk about how much our sister's drive us crazy."

Kate pulls me into her breasts. "Here big brother, take your time, you deserve it, Good boy." Kate says soothingly.

I suckle Kate's perfect rose colored breasts, moaning softly, until she pulls me away a few minutes later.

"Does Chloe know?" Kate asks a moment later.

"No sis, You can't say anything, please sis," I implore her.

"I won't, but you know we are still good friends,"

I nod as she assures me.

"I won't tell big bro, but I might want you to tell Soy boy." Kate pauses before asking, "Is Soy boy small?"

"Not quite as big as," my words trail off as I see my sister's face. "I mean his cock is a bit smaller than my little cock sis."

Kate smiles as I correct myself. "Good boy," she purrs softly, before rolling over and carefully positioning her sweet tits on my aching cock.

Smiling softly, she says, "You can fuck my titties big brother, but Do Not Cum!"

I moan loudly, and begin thrusting my cock into her cleavage. Kate leans over, she opens her mouth, allowing her drool to lube my cock and her boobs.

"Does Soy boy think I am hot, bro?" I nod, as she continues, "and you like Chloe?"

I nod again, and say, "Yeah she is gorgeous too sis."

"Good boy, tell me more about jackin with your friend, to your sister's, Roger."

I spend the next ten minutes telling secrets I had promised never to tell anyone. Moaning as I slide my aching little cock through my sister's cleavage. Her boobs are glazed with my pre cum, my hips are bucking as I fight my orgasm.

Kate can tell I am having trouble, she lifts up, saying, "We will talk more about that later big brother."

"I nod, my eyes locked on her glazed titties.

Kate leans in saying, "here bro, clean me up." I suckle happily, listening to her soft moans. A few minutes later, Kate again has to pull me off.

"Hang on," she says lightly. Kate moves to her bag, retrieving a tape measure. "Of course I have a tape measure big bro," she adds, seeing the surprise in my eyes.

"What size is your little cock again bro,?" Kate leans closer as she asks.

"Um maybe 5 and a half sis," I say quietly

Kate holds the tape against me, adjusting carefully, while I moan from the contact. "Look big bro, you are a full six inches right now. That's how horny you are for your sister."

Kate beams as I look down confirming her measurement.

"Wow sis, how did you?" My words trail off as I look. I had measured myself many times, before coming to terms with my size, or lack thereof. I know I am five and a half inches.

I am shaking my head as I look again at the tape, confirming the tip is at the six inch mark. "My little sister is the world's best cock tease." I say proudly, as Kate smiles and bows.

"I guess your sister adds an inch, you know like TV adds 10 pounds."

Kate just laughs and blows me a kiss. pausing to correct me. "Um half an inch bro, but it's still pretty good." Kate again giggles.

I chuckle softly, still staring at my cock, until Kate brings me back. "Will you be in trouble for telling me about Soy boy Roger?"

I shake my head before replying.

"We always swore we would never tell anyone, but, I think he would understand me telling my half naked sister. So it's okay." I smile,hoping I am right.

"So have you guys talked about fucking us together, or sharing one of us?"

I laugh softly, "Every time we jerk off sis."

"We usually cum imagining our pretty little sister's blowing us in front of each other."

"Or imagining sharing one of you, usually both, it depends how many times we cum," I explain.

"Mmm," Kate moans loudly. "We will discuss that further big bro, but for now roll over, while I grab my toys."

I roll back onto my tummy, my cock throbbing into the bed while I wait.

"Ever had a prostate massage big brother?" Kate asks playfully, while walking towards me with a small bag of toy's, and lube.

"No," I moan nervously, as she giggles.

Kate asks, "You know what that is though?"

I nod my head down, Kate can see I am nervous.

"You are committed to becoming my good boy, Right big bro?"

"I want to be my sister's good boy," I reply.

"Good boy, spread those legs then," another "good boy" follows as I obey.

Kate drips coconut oil onto and into my ass, as she explains.

"There will be days of teasing, days of femdom, and days of reward big brother. Sometimes the teasing will last more than one day, I like big loads. bro." Kate explains smiling softly.

Kate's fingers circle my hole as she adds. "On reward days, you will be glad you waited. You will cum so much, in my mouth, on my tits, anywhere you want big brother."

Kate giggles, listening to me moan. as she adds, "Even inside me big brother."

I let out a series of moans, another moan follows as Kate slides her finger into me, whispering, "Relax big bro, relax."

"Your rewards will be based on how good you are on the other days, big bro." Kate pauses waiting.

"I understand little sis," I reply softly.

"This is a femdom day." Kate begins fucking me with her finger slowly but firmly, as she explains.

"On femdom days, good boys, get to lick up their cummies for me, and swallow." Kate adds another finger, as I moan, "Tell me again big bro."

"I really want to learn to be a good boy for my beautiful little sister." I say promptly. I moan happily as I am rewarded with a harder fingering.

"Now Roger, one last thing, if you are a bad boy and cum before I say so, you have to skip reward day."

"I understand little sis."

Another moan lets me know Kate approves of my answer. "Lift up," she says a moment later, guiding me into doggy position.

Kate gently cups my balls as she fingers me, my moans increasing steadily. "Do you like the way your little sister fingers your tight ass Roger?"

"I love the way my little sister fingers my tight ass Kate."

"Good boy," she responds happily while increasing her pace. "I did this to both of my snuggle buddies too Roger, and more." Kate giggles adding, "I assume you saw the strap on harness big bro?"

My silence causes her to giggle even more, Kate fingers me steadily as her giggles fade. "I would prefer two good boys though, you might have to talk to Soy boy big bro, understood?"

"I understand sis."

My reply turns into a moan as Kate glides her soft hand across my shaft while whispering, "Good boy big brother."

Kate's fingers loosely encircle my shaft. She whispers, "pass me the small pink dildo bro."

"You are so hard big bro, for your sister." Kate sighs, as I retrieve the toy. "I have really needed this big brother, God I miss teasing cock."

Kate begins slowly, inching the dildo into me, cooing gleefully, as she reaches the end. "Good boy, big bro, it's all in you, just relax now."

"I am so wet big brother, you are being a really good boy. I feel so sexy, so powerful. You will do anything for your sister's pussy, won't you big brother?"

"I will do whatever my little sister wants," my reply is strained as I fight my orgasm.

"Good boy," Kate says softly, her hand encircling my twitchy little cock.

I moan as Kate begins to softly stroke my aching cock, almost cumming immediately. "How does your sister's hand feel Roger?" Her voice is sultry drawing out her words.

I moan, replying when I am able, "My sisters hand feels amazing Kate."

"Just relax, don't cum," Kate soothes me, as she strokes me slowly, just holding the dildo in me.

Kate instructs me as she begins to fuck me with her toy. "You are going to want to thrust into my hand big brother, but don't, or you will cum."

"Good boy," Kate whispers, slowly but surely increasing her pace with the dildo, her hand cupping my balls against my shaft. Kate begins sliding her index finger up and down my shaft slowly while fucking me harder and harder.

I am moaning wildly, fighting my urge to fuck Kate's hand, sure my cock will shoot at any second. My legs are shaking as she stretches my tight ass out.

Kate fucks me for a solid five minutes, softly whispering in my ear. "Good boy big brother, good boy." Her fingers expertly edging my little aching cock.

Kate brings me to the edge over and over, using her fingers and the dildo, in concert. Waves of pleasure are shooting from my prostate, into my throbbing cock. I am dripping pre cum like a faucet.

I am in awe, never suspecting I could be this horny. I am moaning wildly.

Kate pushes my head down. "Shh," she whispers softly, before increasing her pace. Kate is thrusting the dildo in and out of my virgin ass, her hand slowly stroking up and down my throbbing shaft.

My cock feels harder than ever before, the pressure is intense. Kate fucks me hard for a few more minutes, still teasing my sore cock.

I am trembling, sure I will cum at any second, screaming to myself in my head, don't cum, don't cum.

I realize I am whimpering, a slow steady stream of "please," coming from me involuntarily. Begging my sister for release. My sister's giggles, her soft moans, her only response to my pleading.